JP2010116398A - 含リン化合物とその製造方法 - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 35
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 34
- 239000011574 phosphorus Substances 0.000 title claims abstract description 32
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- -1 anthraquinonyl Chemical group 0.000 claims abstract description 46
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 125000005427 anthranyl group Chemical group 0.000 claims abstract description 5
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims abstract description 5
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 abstract description 12
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 11
- 229920005992 thermoplastic resin Polymers 0.000 abstract description 4
- 229920001187 thermosetting polymer Polymers 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 8
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 239000003822 epoxy resin Substances 0.000 description 5
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910000410 antimony oxide Inorganic materials 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 239000002648 laminated material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657172—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and one oxygen atom being part of a (thio)phosphinic acid ester: (X = O, S)
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- Molecular Biology (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】下記式(I)に示す構造を有する含リン化合物:
(I)[式中、Arは、炭素原子1〜6個を有するアルキル基、ニトロ基、ハロゲン原子およびフェニル基からなる群より選ばれた基に置換された又は未置換の、ナフチル基、アントラニル基、フェナントリル基、アントラノン基、アントラキノニル基、ビフェニリル基、ジフェニルエーテル基、ジフェニルチオエーテル基、ジフェニルスルホニル基、ジ(フェニル)C1−6アルキル基およびジ(ナフチル)C1−6アルキル基からなる群より選ばれる一つの基の2価基を示し;mとnは、それぞれ独立して1〜5の整数を示す。]
【選択図】なし
Description
(9,10−ジヒドロ−9−オキサ−10−ホスホフェナントレン−10−オキサイド−10−イル)−ジ(4−ヒドロキシフェニル)メタン(HPP)414.4gと、炭酸エチレン(EC)176.1gと、ヨウ化カリウム0.6gと、N−メチルピロリドン1000gとを反応容器中に加え、攪拌、混合した後、150℃に昇温して8時間反応を続け、反応容器中に炭酸ガスが発生しなくなるまで反応を行った。反応終了後、乾燥により溶剤を除き、反応生成物(HPPEC)468gを得た。
(9,10−ジヒドロ−9−オキサ−10−ホスホフェナントレン−10−オキサイド−10−イル)−ジ(4−ヒドロキシフェニル)メタン207.2gと、エポキシエタン45gと、ヨウ化カリウム0.3gと、N−メチルピロリドン500gとを反応容器中に入れ、攪拌、混合した後、150℃に昇温し、反応容器内に炭酸ガスが発生しなくなるまで、8時間反応を行った。反応終了後、乾燥により溶剤を除き、反応生成物として、HPPEO230gを得た。図4に生成物HPPEOのFTIR分析スペクトルを示す。図4より、波長2930cm−1に強い吸収ピークが存在し、−CH2−がHPPとの結合を示し、さらに、波長1251cm−1に強い吸収ピークがあり、フェノールのヒドロキシル基がすでに反応してエーテル基になったことが判る。樹脂の軟化温度は87℃であった。
難燃剤として、HPP1gと、実施例1の生成物HPPEC1gとを、それぞれ溶剤20gに溶かした。その溶解度を表1に示す。
Claims (11)
- 前記Arは、炭素原子1〜6個を有するアルキル基、ニトロ基およびフェニル基からなる群より選ばれた基に置換された又は未置換の、ビフェニリル基およびジ(フェニル)C1−6アルキル基からなる群より選ばれる一つの基の2価基である、請求項1に記載の含リン化合物。
- 前記Arは、2価のビフェニリル基である、請求項1または2に記載の含リン化合物。
- 前記ハロゲン原子は、フッ素、塩素、臭素およびヨウ素からなる群より選ばれるものである、請求項1〜3いずれかに記載の含リン化合物。
- 前記炭素原子1〜6個を有するアルキル基が、メチル基、エチル基、プロピル基、ヘキシル基およびシクロヘキシル基からなる群より選ばれる基である、請求項1〜4いずれかに記載の含リン化合物。
- 前記2価のジ(フェニル)C1−6アルキル基が、2価のジ(フェニル)メチル基、ジ(フェニル)エチル基、ジ(フェニル)プロピル基、ジ(フェニル)ヘキシル基およびジ(フェニル)シクロヘキシル基からなる群より選ばれる基である、請求項1〜5いずれかに記載の含リン化合物。
- 前記2価のジ(ナフチル)C1−6アルキル基が、2価のジ(ナフチル)メチル基、ジ(ナフチル)エチル基、ジ(ナフチル)プロピル基、ジ(ナフチル)ヘキシル基およびジ(ナフチル)シクロヘキシル基からなる群より選ばれる基である、請求項1〜6いずれかに記載の含リン化合物。
- 請求項1に記載の前記式(I)に示す含リン化合物の製造方法であって、
(a)加熱しながら、下記式(II)に示す化合物
[式中、Arは、炭素原子1〜6個を有するアルキル基、ニトロ基、ハロゲン原子、フェニル基より置換された又は未置換の、ナフチル基、アントラニル基、フェナントリル基、アントラノン基、アントラキノニル基、ビフェニリル基、ジフェニルエーテル基、ジフェニルチオエーテル基、ジフェニルスルホニル基、ジ(フェニル)C1−6アルキル基およびジ(ナフチル)C1−6アルキル基からなる群より選ばれる基の2価基を示す。]と、
炭酸アルキルオレフィンエステル又はエポキシアルカンと、を溶剤中で反応を行い;
(b)乾燥により溶剤を除去して、目的の生成物を得る
ことを特徴とする含リン化合物の製造方法。 - 前記炭酸アルキルオレフィンエステルは、炭素原子1〜6個を有するアルキル基、炭素原子1〜6個を有するハロゲン化アルキル基およびハロゲンからなる群より選ばれる基に置換された又は未置換の炭酸エチレンエステルより選ばれるものである、請求項8に記載の含リン化合物の製造方法。
- 前記炭酸アルキルオレフィンエステルは、炭酸エチレンエステル、炭酸プロピレンエステル、フルオロ炭酸エチレンエステル、クロロ炭酸エチレンエステル、5,5−ジエチル−1,3−ジオキシペンタシクロ−ジ−ノンおよび5−メチル−5−プロピル−1,3−ジオキシペンタシクロ−ジ−ノンからなる群より選ばれるものである、請求項8または9に記載の含リン化合物の製造方法。
- 前記エポキシアルカンはエポキシエタンである、請求項8〜10いずれかに記載の含リン化合物の製造方法。
Applications Claiming Priority (2)
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TW097144014A TWI388567B (zh) | 2008-11-14 | 2008-11-14 | 含磷化合物及其製法 |
TW097144014 | 2008-11-14 |
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JP5276571B2 JP5276571B2 (ja) | 2013-08-28 |
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US (1) | US8785696B2 (ja) |
EP (1) | EP2186816B1 (ja) |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012046467A (ja) * | 2010-08-30 | 2012-03-08 | Fushimi Pharm Co Ltd | オリゴ(フェニレンオキシ)基含有環状ホスフィネート化合物およびその製造方法 |
JP2017071775A (ja) * | 2015-10-08 | 2017-04-13 | 長春人造樹脂廠股▲分▼有限公司 | ホスフィン酸化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマー及びその熱硬化性樹脂 |
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TWI307350B (en) * | 2006-01-27 | 2009-03-11 | Chang Chun Plastics Co Ltd | Flame retarding thermoset resin composition |
TWI324168B (en) * | 2006-03-17 | 2010-05-01 | Chang Chun Plastics Co Ltd | Flame retarding thermoset epoxy resin composition |
TWI380991B (zh) * | 2007-12-28 | 2013-01-01 | Chang Chun Plastics Co Ltd | 磷系苯並噁嗪化合物及其製備方法 |
TWI397533B (zh) * | 2008-04-11 | 2013-06-01 | Chang Chun Plastics Co Ltd | 新穎磷系化合物及其製造方法及用途 |
TWI359151B (en) * | 2008-07-02 | 2012-03-01 | Chang Chun Plastics Co Ltd | Phosphorus-containing compounds and their preparat |
TWI449707B (zh) * | 2008-07-15 | 2014-08-21 | Univ Nat Chunghsing | 新穎磷系雙酚及其衍生物之製造方法 |
TW201016716A (en) * | 2008-10-23 | 2010-05-01 | Chang Chun Plastics Co Ltd | Phosphorus-containing compound and manufacturing method thereof |
TWI382035B (zh) * | 2010-01-13 | 2013-01-11 | Chang Chun Plastics Co Ltd | 磷系環氧樹脂半固化物及其製備方法 |
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Cited By (3)
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JP2012046467A (ja) * | 2010-08-30 | 2012-03-08 | Fushimi Pharm Co Ltd | オリゴ(フェニレンオキシ)基含有環状ホスフィネート化合物およびその製造方法 |
JP2017071775A (ja) * | 2015-10-08 | 2017-04-13 | 長春人造樹脂廠股▲分▼有限公司 | ホスフィン酸化ポリ(2,6−ジメチルフェニレンオキシド)オリゴマー及びその熱硬化性樹脂 |
US10544261B2 (en) | 2015-10-08 | 2020-01-28 | Chang Chun Plastics Co., Ltd. | Phosphinated poly(2,6-dimethyl phenylene oxide) oligomers and thermosets thereof |
Also Published As
Publication number | Publication date |
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TW201018699A (en) | 2010-05-16 |
JP5276571B2 (ja) | 2013-08-28 |
EP2186816A1 (en) | 2010-05-19 |
TWI388567B (zh) | 2013-03-11 |
US20100125154A1 (en) | 2010-05-20 |
US8785696B2 (en) | 2014-07-22 |
EP2186816B1 (en) | 2014-01-01 |
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